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Cannabichromene

CAS# 20675-51-8

Cannabichromene

2D Structure

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Quality Control of Cannabichromene

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Cannabichromene

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Chemical Properties of Cannabichromene

Cas No. 20675-51-8 SDF Download SDF
PubChem ID 30219 Appearance Oil
Formula C21H30O2 M.Wt 314.5
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromen-5-ol
SMILES CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1)O
Standard InChIKey UVOLYTDXHDXWJU-UHFFFAOYSA-N
Standard InChI InChI=1S/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Cannabichromene

The herb of Cannabis sativa.

Biological Activity of Cannabichromene

Description1. Cannabichromene is a major non-psychotropic phytocannabinoid that inhibits endocannabinoid inactivation and activates the transient receptor potential ankyrin-1 (TRPA1), it selectively reduces inflammation-induced hypermotility in vivo in a manner that is not dependent on cannabinoid receptors or TRPA1. 2. Cannabichromene exerts anti-inflammatory actions in activated macrophages with tonic CB1 cannabinoid signalling being negatively coupled to this effect and ameliorates experimental murine colitis. 3. Cannabichromene can raise the viability of neural stem progenitor cells (NSPCs), while inhibiting their differentiation into astroglia, possibly through up-regulation of ATP and adenosine signalling.
TargetsNOS | COX | ERK | ATPase

Cannabichromene Dilution Calculator

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Cannabichromene Molarity Calculator

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Preparing Stock Solutions of Cannabichromene

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1797 mL 15.8983 mL 31.7965 mL 63.593 mL 79.4913 mL
5 mM 0.6359 mL 3.1797 mL 6.3593 mL 12.7186 mL 15.8983 mL
10 mM 0.318 mL 1.5898 mL 3.1797 mL 6.3593 mL 7.9491 mL
50 mM 0.0636 mL 0.318 mL 0.6359 mL 1.2719 mL 1.5898 mL
100 mM 0.0318 mL 0.159 mL 0.318 mL 0.6359 mL 0.7949 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Cannabichromene

The cannabinoid TRPA1 agonist cannabichromene inhibits nitric oxide production in macrophages and ameliorates murine colitis.[Pubmed:23373571]

Br J Pharmacol. 2013 May;169(1):213-29.

BACKGROUND AND PURPOSE: The non-psychotropic cannabinoid Cannabichromene is known to activate the transient receptor potential ankyrin-type1 (TRPA1) and to inhibit endocannabinoid inactivation, both of which are involved in inflammatory processes. We examined here the effects of this phytocannabinoid on peritoneal macrophages and its efficacy in an experimental model of colitis. EXPERIMENTAL APPROACH: Murine peritoneal macrophages were activated in vitro by LPS. Nitrite levels were measured using a fluorescent assay; inducible nitric oxide (iNOS), cyclooxygenase-2 (COX-2) and cannabinoid (CB1 and CB2 ) receptors were analysed by RT-PCR (and/or Western blot analysis); colitis was induced by dinitrobenzene sulphonic acid (DNBS). Endocannabinoid (anandamide and 2-arachidonoylglycerol), palmitoylethanolamide and oleoylethanolamide levels were measured by liquid chromatography-mass spectrometry. Colonic inflammation was assessed by evaluating the myeloperoxidase activity as well as by histology and immunohistochemistry. KEY RESULTS: LPS caused a significant production of nitrites, associated to up-regulation of anandamide, iNOS, COX-2, CB1 receptors and down-regulation of CB2 receptors mRNA expression. Cannabichromene significantly reduced LPS-stimulated nitrite levels, and its effect was mimicked by cannabinoid receptor and TRPA1 agonists (carvacrol and cinnamaldehyde) and enhanced by CB1 receptor antagonists. LPS-induced anandamide, iNOS, COX-2 and cannabinoid receptor changes were not significantly modified by Cannabichromene, which, however, increased oleoylethanolamide levels. In vivo, Cannabichromene ameliorated DNBS-induced colonic inflammation, as revealed by histology, immunohistochemistry and myeloperoxidase activity. CONCLUSION AND IMPLICATIONS: Cannabichromene exerts anti-inflammatory actions in activated macrophages - with tonic CB1 cannabinoid signalling being negatively coupled to this effect - and ameliorates experimental murine colitis.

Inhibitory effect of cannabichromene, a major non-psychotropic cannabinoid extracted from Cannabis sativa, on inflammation-induced hypermotility in mice.[Pubmed:22300105]

Br J Pharmacol. 2012 Jun;166(4):1444-60.

BACKGROUND AND PURPOSE: Cannabichromene (CBC) is a major non-psychotropic phytocannabinoid that inhibits endocannabinoid inactivation and activates the transient receptor potential ankyrin-1 (TRPA1). Both endocannabinoids and TRPA1 may modulate gastrointestinal motility. Here, we investigated the effect of CBC on mouse intestinal motility in physiological and pathological states. EXPERIMENTAL APPROACH: Inflammation was induced in the mouse small intestine by croton oil. Endocannabinoid (anandamide and 2-arachidonoyl glycerol), palmitoylethanolamide and oleoylethanolamide levels were measured by liquid chromatography-mass spectrometry; TRPA1 and cannabinoid receptors were analysed by quantitative RT-PCR; upper gastrointestinal transit, colonic propulsion and whole gut transit were evaluated in vivo; contractility was evaluated in vitro by stimulating the isolated ileum, in an organ bath, with ACh or electrical field stimulation (EFS). KEY RESULTS: Croton oil administration was associated with decreased levels of anandamide (but not 2-arachidonoyl glycerol) and palmitoylethanolamide, up-regulation of TRPA1 and CB(1) receptors and down-regulation of CB(2) receptors. Ex vivo CBC did not change endocannabinoid levels, but it altered the mRNA expression of TRPA1 and cannabinoid receptors. In vivo, CBC did not affect motility in control mice, but normalized croton oil-induced hypermotility. In vitro, CBC reduced preferentially EFS- versus ACh-induced contractions. Both in vitro and in vivo, the inhibitory effect of CBC was not modified by cannabinoid or TRPA1 receptor antagonists. CONCLUSION AND IMPLICATIONS: CBC selectively reduces inflammation-induced hypermotility in vivo in a manner that is not dependent on cannabinoid receptors or TRPA1.

Cannabichromene and tetrahydrocannabinol determination in mouse blood and brain by gas chromatography-mass spectrometry.[Pubmed:21871159]

J Anal Toxicol. 2011 Sep;35(7):496-500.

Cannabichromene (CBC) is a phytocannabinoid, the second most abundant cannabinoid quantitatively in marijuana. CBC has been shown to produce antinociception and anti-inflammatory effects in rodents. This method is validated for the measurement of THC and CBC simultaneously after extraction from mouse blood or brain. Whole brain harvested from mice was homogenized 2:1 (v/w) with normal saline. Fifty nanograms of THC-d(3) was added to 0.5 mL of heparinized mouse blood, brain homogenate, and THC and CBC fortified blood or brain calibrators, then equilibrated overnight at 5 degrees C. Two milliliters of "ice cold" acetonitrile was added drop-wise while the sample was vortex mixed, and then the sample was centrifuged and stored overnight at -30 degrees C. The cannabinoids were extracted from the acetonitrile layer with 2 mL of 0.2 N NaOH and 4 mL of hexane/ethyl acetate (9:1). The solvent was isolated and evaporated to dryness. Trimethylsilyl derivatives were prepared and then analyzed by gas chromatography-mass spectrometry. Linearity in blood and brain of THC and CBC was 2-10,000 ng/mL (ng/g). THC and CBC recovery ranged from 56 to 78% in blood and brain. Precision was demonstrated at 100 ng/mL and 1000 ng/mL with CVs < 15%. The validated method allows for blood and brain concentrations of cannabinoids to be quantificated and correlated with pharmacological effects produced in mice.

The effect of cannabichromene on adult neural stem/progenitor cells.[Pubmed:23941747]

Neurochem Int. 2013 Nov;63(5):432-7.

Apart from the psychotropic compound Delta(9)-tetrahydrocannabinol (THC), evidence suggests that other non-psychotropic phytocannabinoids are also of potential clinical use. This study aimed at elucidating the effect of major non-THC phytocannabinoids on the fate of adult neural stem progenitor cells (NSPCs), which are an essential component of brain function in health as well as in pathology. We tested three compounds: cannabidiol, cannabigerol, and Cannabichromene (CBC), and found that CBC has a positive effect on the viability of mouse NSPCs during differentiation in vitro. The expression of NSPC and astrocyte markers nestin and Glial fibrillary acidic protein (GFAP), respectively, was up- and down-regulated, respectively. CBC stimulated ERK1/2 phosphorylation; however, this effect had a slower onset in comparison to typical MAPK stimulation. A MEK inhibitor, U0126, antagonized the up-regulation of nestin but not the down-regulation of GFAP. Based on a previous report, we studied the potential involvement of the adenosine A1 receptor in the effect of CBC on these cells and found that the selective adenosine A1 receptor antagonist, DPCPX, counteracted both ERK1/2 phosphorylation and up-regulation of nestin by CBC, indicating that also adenosine is involved in these effects of CBC, but possibly not in CBC inhibitory effect on GFAP expression. Next, we measured ATP levels as an equilibrium marker of adenosine and found higher ATP levels during differentiation of NSPCs in the presence of CBC. Taken together, our results suggest that CBC raises the viability of NSPCs while inhibiting their differentiation into astroglia, possibly through up-regulation of ATP and adenosine signalling.

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